| Synthesis and structure-activity relationship studies of cinnamic acid-based novel thiazolidinedione antihyperglycemic agents. | |
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MedLine Citation:
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PMID: 12927868 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A number of 2,4-thiazolidinedione derivatives of -phenyl substituted cinnamic acid were synthesized and studied for their PPAR agonist activity. The E-isomer of cinnamic acid, 11, showed moderate PPAR transactivation. The corresponding Z-isomer, 23, and double bond reduced derivative, 15, were found to be much less potent. Although the E-isomer showed a moderate PPAR gamma transactivation, it demonstrated a strong glucose-lowering effect in a genetic rodent model of diabetes. Results of pharmacokinetic, metabolism and permeability studies are consistent with 11 being an active prodrug with an active metabolite, 14, that has similar glucose lowering and PPAR gamma agonist properties. |
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Authors:
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Partha Neogi; Fredrick J Lakner; Satyanarayana Medicherla; Jin Cheng; Debendranath Dey; Maya Gowri; Bishwajit Nag; Somesh D Sharma; Lesley B Pickford; Coleman Gross |
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Publication Detail:
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Type: Comparative Study; Journal Article |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 11 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2003 Sep |
Date Detail:
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Created Date: 2003-08-20 Completed Date: 2004-11-09 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 4059-67 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Calyx Therapeutics Inc., 3513 Breakwater Avenue, Hayward, CA 94545, USA. p.neogi@att.net |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Blood Glucose / analysis, metabolism Cinnamates / chemistry* Diabetes Mellitus, Type 2 / drug therapy, metabolism Disease Models, Animal Hypoglycemic Agents / chemical synthesis*, pharmacology, therapeutic use Isomerism Mice Phenylpropionates / chemical synthesis, pharmacology Prodrugs / chemical synthesis, pharmacology Receptors, Cytoplasmic and Nuclear / agonists, biosynthesis Structure-Activity Relationship Thiazolidinediones / chemical synthesis*, pharmacology, therapeutic use Transcription Factors / agonists, biosynthesis |
| Chemical | |
Reg. No./Substance:
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0/Blood Glucose; 0/Cinnamates; 0/Hypoglycemic Agents; 0/Phenylpropionates; 0/Prodrugs; 0/Receptors, Cytoplasmic and Nuclear; 0/Thiazolidinediones; 0/Transcription Factors; 621-82-9/cinnamic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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